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The Executive AI Briefing for Busy Leaders

Welcome to Lead with AI, the only executive AI brief for busy leaders.

Every edition, I deliver the latest AI updates through real-world insights and discussions from our ​community​ of 150+ forward-thinking executives.

In this week's edition, I want to focus on:

AI as a Thinking Partner

There have been so many updates to the AI models recently, that the question of which platform to choose is becoming increasingly complicated to answer.

For you, as a senior leader, I want you to think about it through a lens you may not have thought about yet.

Last Friday, we wrapped up the 3rd and final live session of Lead with AI Cohort 6.

While few business leaders enter this program expecting it, one concept is starting to stand out as transformative for them: AI's power as a thinking partner.

It's all this group could talk about. Rather than a 'tool' that can help you work faster, AI became a collaborative partner for these business leaders.

One that allows them to think more clearly, make better decisions, and explore creative solutions in ways previously unimaginable.

Shifting Perspectives: AI as a Coworker, Not a Tool

For many executives, the first breakthrough is realizing that AI isn't just software for automating repetitive tasks.

For many course participants, this starts with assigning "personalities" or roles to AI—for instance, using it as a communications strategist, a psychology consultant, or even a product design coach.

This shift, from basic prompting to CO-DO "SuperPrompting" (which you can generate with our ChatGPT Prompt Generator here) reframes how leaders engage with AI, encouraging more dynamic and meaningful collaboration by treating AI as a coworker, not a tool.

But the real unlock for many people I've trained over the past year is treating AI like a senior thinking partner.

By tapping into AI's vast 'brain,' it can act as an interactive advisor, like a senior colleague, mentor, or executive coach. The value of this is (unsurprisingly) immense.

Rather than simply asking AI for answers, leaders are learning to engage in a dialogue, guiding the AI through iterative problem-solving.

For example, by not asking for answers, but challenging AI to ask them better questions. After all, sometimes a good question delivers better results than a quick answer.

Ethan Mollick’s Take: Frontier Models and Reasoning Power

Ethan Mollick, a leading voice on practical AI adoption, echoes this sentiment in his latest guide on today’s top AI tools, which I also shared in our community.

He highlights that the most advanced models, like OpenAI’s GPT-4o, Anthropic’s Claude 3.5, and Google’s Gemini 2.0, are no longer just powerful—they’re thoughtful. (The same goes for the latest disrupter, Deepseek. More on that in tomorrow's Stay Ahead newsletter.)

Mollick describes the rise of reasoning models, which excel at tackling complex, multi-step problems by “thinking” before responding.

These models, such as OpenAI’s o1 series, can act like scholars or advisors, providing well-reasoned answers that feel eerily human. For executives, this capability is invaluable.

Whether solving intricate business challenges or running simulations, reasoning models elevate AI from a reactive assistant to a proactive thought partner.

He also praises AI’s Live Mode features, such as ChatGPT’s Advanced Voice Mode, which integrates real-time voice and visual inputs. (For me, the ultimate game-changer.)

This enables seamless, natural interactions, creating the sense of engaging with a knowledgeable and intuitive collaborator. It's a feature that fundamentally change how much value many of the leaders I work with get out of AI.

Lightbulb Moments from Executives

In the cohort, many leaders experienced their own “lightbulb moments.”

One participant described how voice-based interactions with AI sparked a deeper sense of collaboration, making it feel like brainstorming with an insightful coworker.

Others shared how assigning specific roles to AI—like “customer success strategist” or “business development coach”—helped unlock fresh perspectives on familiar challenges.

Executives are also finding that AI helps them balance automation with intuition.

While AI excels at handling repetitive or data-driven tasks, leaders still bring the judgment and creativity required for higher-order decisions.

By offloading supporting processes to AI, they’re freeing up time to focus on the strategic questions only humans can answer, something that's crucial to underscore for successful AI implementations.

Experimentation Is Key

Both in the Lead with AI program and in Mollick’s guide, one takeaway is clear: you need to experiment.

AI’s potential isn’t fully realized until you actively engage with it—whether it’s testing different tools, exploring use cases, or customizing it for your workflows.

For example, tools like ChatGPT’s custom GPTs and Gemini’s Google Workspace integrations (I've been very impressed by some of the recent updates) allow for tailored solutions that align with specific business needs.

And while AI capabilities are evolving at breakneck speed, the secret isn’t waiting for the “perfect” system. It’s diving in now and discovering how AI can complement your thinking and decision-making. (See more AI change management best practices.)

What This Means for Leaders

As AI evolves, the leaders who embrace it as a thinking partner will gain a significant edge. The ability to work alongside AI—to brainstorm, analyze, and strategize—will define tomorrow’s most effective executives.

So, ask yourself: How could AI support your next big decision or creative project? If the Lead with AI cohort has shown us anything, it’s that the future of leadership isn’t about competing with AI. It’s about partnering with it.

Want to get started?

I'm happy to share a few practical tips – just reply to this email, and I'll help out.

Until next week,

– Daan

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“Your AI Team” Platform Updates

Essential updates from our core AI platforms can mean big changes in your and your team's productivity. Here's what's new from the essential AI tools that most Lead with AI leaders are using:

ChatGPT Operator Kickstarts "The Year of Agents."

As fellow FlexOS Creator Antony Slumbers recently wrote, 2025 is the year of agents. Well, OpenAI is clearly taking this whole movement seriously.

Last Thursday, the company launched "Operator," an AI agent capable of performing tasks on the web, such as booking trips and purchasing groceries.

Operator interacts with web pages by interpreting commands and operating a web browser, automating personal and professional tasks. (It does ask for user confirmation before taking irreversible actions like purchases!)

Initially available for Pro users at $200 per month, Operator will likely eventually be part of the core ChatGPT experience. This means serious disruption for 'business as usual.'

As a leader, start thinking about the implications of true "agentic" work:

  • How could Operator reshape the balance between human and AI-led decision-making in your organization, and what new opportunities or risks could this bring?
  • Which high-friction processes in your business—like procurement, compliance, or customer service—could be reimagined with Operator’s automation capabilities, and how would this impact your workforce?
  • What ethical and governance frameworks do you need to implement to ensure Operator operates as a trusted assistant rather than a potential liability in sensitive operations?

The Verge has a good breakdown of Operator's capabilities, read it here.​

AI Automations for Google Workspace

Recently introduced as an alpha feature for Business, Enterprise, and Education plans, Gemini now brings AI-powered workflows directly into Gmail on the web.

Here’s how it works: when Gemini detects a task it can help with—like saving receipts to Drive, tracking them in Sheets, or drafting replies to customer queries—it suggests a prompt.

Clicking the prompt opens a side panel where Gemini assists with the task. You can even automate recurring actions, letting Gemini handle them in the future without extra input.

I used this for customer service and found it extremely helpful and a true time saver. (If you want details, let me know.)

This is another glimpse at how AI might transform routine workflows. Read the details here and try it yourself if you're a Google user.

Reminder: Google Workspace AI and Microsoft Copilot

Both Google and Microsoft decided to nix the $20+ monthly fees and rather bake AI features into their product sets.

It may take some time to roll out, but expect many more of your team members to get access to these features (and have questions about them.

Find out more here to ensure you're prepared:

(More AI news after this break!)
Available Now

This Newsletter is Free. But Falling Behind on AI Can Be Costly.

I've been speaking to too many business leaders who feel behind on AI.

Are you watching others master AI while you wonder how to start?

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How Companies Implement AI

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The AI Executive Brief

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  • Deepseek, the Chinese AI that beat US rivals in many ways, is the talk of the town in Silicon Valley. This 45-minute CNBC feature tells you all that you need to know.
  • $500 billion is what Stargate, a new partnership between OpenAI, Oracle, and SoftBank, will invest in data centers and other AI initiatives.
    • xAI CEO Elon Musk, however, was quick to point out that "they don't have the money."
    • Not to be outdone, Meta announced that it would invest $65 billion in itself, mostly in data centers.
  • AI Training is key, says Google, which will invest $120 million in AI education programs and partner with colleges to train workers to shape policy and public perception as it is about addressing workforce displacement.
  • President Trump revoked Biden's 2023 executive order requiring AI developers to share safety test results for high-risk systems. In summary, more innovation, fewer safeguards.​
  • AI Agents: NFX previously predicted the "Three-Person Unicorn" and last week shared a new essay about the "Five Stages of AI Agent Evolution" Given what I wrote above about Operator, it is a fascinating framework.
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Every day, our Lead with AI PRO community discuss practical ways to benefit from AI in their work and organizations.

This week's highlights include:

  • Alignerr: the community discussed Alignerr, a platform where you can make money by training models. The consensus? Probably not worth risking.
  • EU and AI: We discussed the Trump / Stargate investment. Many, including Henrik, felt like the EU is now simply a bystander. And, that the US will need to invest heavily in power to supply data centers.
  • AI for LinkedIn Content: Evelyn shared her tutorial for creating LinkedIn posts from long-form content. Read it here and set it up for yourself!
  • AI vs. Engineers: Wyatt shared an article about how AI may start replacing engineers soon in reply to a comment from Joe about how the AI labs must be using their own technology to code at hyperspeed.
  • AI for Charts: I shared several new updates to Napkin AI, one of our community's favorite tools (it creates amazing charts and graphs from a prompt!)
  • Social Bots: Anastasia shared an insightful article about how bots are infiltrating our social platforms - and how we may be engaging with them.
  • Writing with AI: Carlo posted a fascinating video about how one writer utilizes AI as a strategic partner.
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If you made it this far, reply and tell me what you'd love AI to take over in your daily workflow.

Also, please forward this newsletter to a colleague and ask them to subscribe.

If you have any other questions or feedback, just reply or inbox me.

See you next week,

Daan van Rossum - Lead with AI

Daan van Rossum​

Host, Lead with AI